


Better than the First Time

by NaughtyPastryChef



Series: Orgasms For Everyone! spn Kinktober 2017 [31]
Category: Supernatural, Supernatural RPF
Genre: Anal Fingering, Anal Sex, Barebacking, Characters Writing Fanfiction, Dirty Talk, First Kiss, First Time, M/M, Mentions of Underage, Shotgunning, role play
Language: English
Status: Completed
Published: 2017-11-01
Updated: 2017-11-01
Packaged: 2019-01-27 16:42:13
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,054
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12586204
Author URL: https://archiveofourown.org/users/NaughtyPastryChef/pseuds/NaughtyPastryChef
Summary: kinktober day 31 prompt: choose your own. Jared reads more fanfiction and he and Jensen remember and recreate their first time as they have a first time of their own.





	Better than the First Time

**Author's Note:**

  * For [dollylux](https://archiveofourown.org/users/dollylux/gifts), [saltandbyrne](https://archiveofourown.org/users/saltandbyrne/gifts), [waywardelle](https://archiveofourown.org/users/waywardelle/gifts), [Edwardina](https://archiveofourown.org/users/Edwardina/gifts), [bewarethesmirk](https://archiveofourown.org/users/bewarethesmirk/gifts).
  * Inspired by [Learning from Fanfiction](https://archiveofourown.org/works/12178476) by [NaughtyPastryChef](https://archiveofourown.org/users/NaughtyPastryChef/pseuds/NaughtyPastryChef). 



> whoooooaaaaa holy shit. I did it. I FUCKING DID IT. 31 fics in 31 days totaling 28,623 words. Too many people to thank for helping me finish this. But mostly to all the wonderful people who encouraged me with kudos and comments. BLESS YOU ALL. This will make more sense if you read "Learning From Fanfiction" first, but I think it can stand alone. See ending notes for more information.

Despite Jensen’s insistence that they were going to try more and have Jared learn about the less vanilla things in life, they were taking it slow. It was too important and too intense for both of them to rush into things. They worked during the day and made out at night and slept in the same bed and waited. Waited for the right time. Waited for time off. Hiatus was coming soon. But Jared was impatient.

Jared found himself deep in the online fanfiction Supernatural fandom rabbit hole after that first time with Jensen. He made an account on all the sites that he could. He bookmarked his favorite stories. He left kudos and comments on everything he read. He began to engage with these writers, and he found them to be amazing people.

He read the odd long story: backstories of Sam and Dean and how they finally came together. Sometimes he liked to while away his lonely hours reading the angst and heartbreak and love between the brothers. [Invisible Boy is a fic universe](http://archiveofourown.org/works/1017905) that he’d come across numerous times and finally sat down to read the whole series, totally hooked from the first paragraph of the story. The writer had written Sam so well that he was shocked every time he remembered it wasn’t what had happened in the show; privately, he figured he could believe whatever he wanted about them before the show started and he liked that fic. He liked that one a lot.

There was another one too, something called a curtain fic called [The King and the Lionheart](http://archiveofourown.org/works/7421695/chapters/16857040), where Sam and Dean retired to a small New England town and made a life for themselves there. Something about that one rang so true and plucked at his heartstrings so much that he cried while reading it. He wanted that for Sam and Dean; they deserved it. 

He fell in love with Sam and Dean all over again through the eyes of these incredible writers.

But the ones that he read the most, the ones that he felt a little ashamed for reading, were the ones that were just plain porn. Unaderage, first time “teach me how to kiss/jerk off/please you in bed, Dean” porn. He learned a lot about himself as he read the kinky things that these writers dreamed up. He loved the ones that had them younger--pre-series he thought they were called-- and even the fact that Sam was technically underage in all of them didn’t put him off. These authors had Sam being feminized by Dean, Dean calling Sam all kinds of names like “pretty girl” and talking about Sam’s pussy. Jared hadn’t even seen porn so filthy.

[There was one that was focused on scent kink](http://archiveofourown.org/works/522577): Dean coming home from a date and telling Sam all about it while Sam sniffed at him. And, later, Sam couldn’t stop sniffing and huffing and licking at Dean’s armpit as Dean “taught” him about jerking off and cleaning the pipes.

First times. Craving each other. Coming together after the build of tension and doing it despite all the reasons they shouldn’t and sometimes  _ because  _ of the reasons they shouldn’t.

Incest kink was weird and conflicting.

But all along while he was reading and commenting and waiting for his time with Jensen he forgot something important: Jensen read fic too. Jensen knew his screen name for all the sites. He never thought that Jensen would be waiting for him to make the first (second?) move towards more. He didn’t think about the fact that Jensen might find the same things he found. Neither of them thought that taking the next step through wincest would make it all that much easier.

He’d been zoning out all day, thinking about the fic he’d read just before bed last night. [The one where little fifteen year old Sammy was jealous of the girl that worked at the diner cause she got so much of Dean’s attention.](http://archiveofourown.org/works/1007023) They got back to wherever they were staying and Sam had a bitch fit when Dean turned the tables, starting telling Sam what a sweet girl he was and asking, begging, to get into Sam’s panties. To stick his face in Sammy’s sweet pussy. Rimming again, Jared thought. It made sweat prickle on his scalp. It made him uncomfortably hard in his jeans. It made him second guess every single move he made on set all day, both as Jared and as Sam.

They stumbled out of the car and into the house, letting the dogs out and each of them getting comfy while comfortably moving around each other and pulling together a dinner, of sorts. They were settled onto the couch with beers and the remains of their pauper’s supper when Jensen cleared his throat.

“You think Dean was the one that got Sammy’s cherry?”

Jared sputtered and coughed out the sip of beer he’d just taken, glancing over at Jensen to see the Cheshire grin that he knew so well.

“... Maybe. I dunno, really, hadn’t thought much about it.” He felt his face flame at the lie. Not only had he thought about it, he’d jerked off to the thought of it. And Jensen knew it.

“Jay.” He admonished and Jared knew he was caught in the lie.

“Yeah okay. Been reading fan fiction again. It’s fucking hot, alright? Stuff I’ve never heard of, let alone done. And yeah, I think Sam saved his cherry for Dean.” He took another long sip of his beer and focused, as best as he could, on the tv. Jensen stayed quiet.

“What about all the stuff we talked about before? The Pegging stuff with Jess?”Jared thought about it silently for a moment and then, abruptly, his mind went to a scene from Invisible Boy where Sam and Dean’s girlfriend got overly up close and personal while Dean was fucked-out in the next room.

“That’s not the same.”

“And why do you say that?” Jensen sounded actually curious and so Jared tried to put it into words.

“Toys.. might be used as an extension of the body but they aren’t body parts. And, like, fingering is intimate, I get that, but you can do it to yourself? I dunno, in my head, it’s not the same.” He left out the fact that his head was Sam’s head, but he figured that part didn’t need to be said aloud to be understood. “Plus… you know, maybe it was before Jess?”

“Before Jess? But that would have been…” Jensen trailed off but Jared could see his mind working, coming to the same conclusion that he came to. Yeah, Dean popped Sam’s cherry and yeah, it happened before Stanford.

“So… no one else but me Sammy?” Jensen’s voice dropped down to Dean’s timbre and Jared shivered. He tried to take another sip of beer, but his bottle was empty, and took his time placing it beside the leg of the sofa to buy himself time to get under control before replying.

“It’s always been yours Dean. I never wanted anyone else like I want you. Like… like it’s gonna eat me up.” He stayed passive as Jensen moved towards him on the couch.

“You remember how it happened?” Jared’s eyes flew open and he looked at Jensen with his head cocked to the side, considering. Jensen looked like he was asking Jared to tell him a story. Jensen wanted the scenario.

“Course I remember Dean.” He fumbled to buy himself some time to think. He mashed a lot of his favorite stories together in his head, took a deep breath and started to talk.

“You thought you were just teaching me how to jerk off. “Cleanin the pipes” is what you called it. BUt you kept touching me and I couldn’t stop - “ HIs eyes closed and his throat constricted with some emotion he hadn’t been aware of. He felt fingers gripping his chin and opened his eyes.

“Couldn’t stop thinking about your hands on me. What it might be like if you wanted me the way you wanted all those girls.” He took another fortifying breath and felt Jensen’s hand slide up inside his shirt to rest on his stomach.

“So the next time we moved, I bought that bag of weed off some loser at school.” 

Jensen huffed out a shocked laugh. “Sammy, my little rebel. I’d almost forgotten that. Remember you comin home from school, all twitchy and nervous but sweet at the same time. Askin if we could go get a pizza and find a field to sit out and watch the stars.” Jensen smiled as though he was really remembering it and moved impossibly closer on the couch.

“So we went out. I was sweating the whole time with that bag of weed in my pocket and a tape of the remastered Zep’s Mothership I’d bought for you.” He took a chance and darted forward to press a kiss to the soft skin beneath Jensen’s ear. “I never knew that you thought that whole night but it was a date to me.” His voice was low with want as he whispered the words into Jensen’s ear before placing another kiss, lower on his neck.

“You big girl. When we got to that field and parked the car you were no nervous that you’d started to be kinda bitchy. I was ready to call the whole thing off and head back to the hotel when you pulled out the tape and the weed.”  Jensen smiled and pressed a kiss to the corner of Jared’s lips.

“That was the first time we shotgunned too. I still remember the taste of the weed. The feel of the hot smoke in my lungs as I pushed it into your mouth.” He paused, swallowed, and continued, “the feel of your lips against mine.”

Jared shifted, pulling Jensen on top of him and loving the feel of the heavy body on top of his own. He could almost smell the sticky smoke; almost hear Zepplin playing in the background. He looked up into Jensen’s eyes and stretched his neck out, lips parted for a kiss. Jensen dove in tongue first. It was hot, wet, and perfect. Jared arched his hips up, rubbing his dick against the answering hardness in Jensen’s pants before breaking away from the kiss with a low moan.

“Deeeeaaaan.”

“Fuck, Sammy, the things you do to me. You remember? The sound of D’Yer Mak’er in the background as we tried to fit into Baby’s backseat? Even at fifteen you were all goofy long limbs. Prettiest thing I ever saw.” Jensen stopped talking for another searing kiss. Jared felt Jensen move above him again as he broke their kiss, tearing his shirt off over his head.

“You wouldn’t fuck me though.” Jared said as he lay back down after pulling his own shirt off. Jensen froze above him.

“Too special. You’re too fuckin special to waste on a quicky in the back seat.” Jensen was gazing down at him in a pushup position, his arms tensed and muscles bulging. Jared trailed his fingers down Jensen’s bicep from shoulder to elbow.

“Gonna let me into your panties this time, hmm? My pretty Sammy.” Jensen let his whole body come down on top of Jared again.

“Wanted it though. Wanted you inside me. Couldn’t think of anything else for so long. And you were so beautiful Dean. Always were and always will be.” Jensen groaned and crashed their mouths together again.

“You were too big for the backseat then and you’re too big for the couch now. C’mon Sammy. Bed.” Jensen shoved himself off Jared and off the couch and held out a hand to help Jared up. They couldn’t keep their hands off each other as they stumbled through the house, divesting of the last pieces of clothing and bumping into walls. 

Finally they were in the bedroom and Jensen shoved Jared down on his back and crawled up between his spread legs. He grazed his hands up the outside of Jared’s thighs until his palms rested on the cut of Jared’s hips.

“Damn baby boy, you grew up nice. Gonna let me inside you?” Jensen asked and Jared felt his breathing pick up. Jensen was sexy and funny and charming but Dean, Dean who was in bed with him and looking down at him like a fine meal, he was other worldly.

“Dean.” It seemed to be the only word in Jared’s vocabulary at that point. He watched, invested and yet detached, as Jensen lifted his legs at the knee and folded them up until they were pressed to his chest, exposing his hole. He felt more naked in that moment than ever before.

“Need me to eat you out to get you ready, baby? Wanna get my mouth on that sweet hole to get it ready for my cock? Look at that sweet little pussy.” Jensen wasn’t looking at Jared’s face anymore; he was totally focused on Jared’s ass.

Jared felt himself clench and relax at the scrutiny and Jensen groaned like he was dying. “You gotta hold your legs for me Sammy. Just need a taste.” And he dove down, giving wet and sloppy kisses to Jared’s cock and balls, trailing his tongue down his perineum and to his hole. It was totally overwhelming and Jared forgot himself in a rush to get a hand on his dick and pump it, nearly kicking Jensen off the bed as he kicked him when he let go of his legs.

“I don’t want it rough this time, Sammy. Maybe next time.” Jensen joked. Jared flung out a hand to reach his bedside table, he’d had enough teasing. Enough torture. He pulled open the drawer so hard that half the contents ended up on the floor but his fingers closed around the bottle of lube he’d stashed there before it fell.

“Dean, please.” He begged, shoving the bottle into Jensen’s hands and lifting his legs to hold himself open. He could see the way that Jensen’s eyes darkened and his chest heaved with breath. “Don’t wanna wait anymore. Don’t wanna remember. Wanna do it. Need you to fuck me Dean.” Jared knew he was whining in Sam’s tone of voice.

“Sammy.” Dean was gasping now, his fingers already slick and heading towards Jared’s ass.

Jared didn’t whine at the first touch, didn’t move, didn’t breathe. He held his breath so that he could hear the way Jensen’s fingers sounded as they slipped inside of him. Soon the sound of his own heartbeat in his ears was too loud and he let out his breath in a great heave. He wiggled his hips and tightened around Jensen’s fingers. The rest of the prep was a blur of too-loud breathing and heart beats throbbing through his whole body so loud that his ears were ringing.

“Nownownownow Deeeee.” He whined. He had no idea how many fingers were inside of him, but he felt wet and open and ready. He needed more. His head tossed back and forth on the pillow with eyes squeezed closed.

“Okay baby boy. I got you. No more waiting.” Jensen crooned, pulling his fingers out with a wet squelch. Jared felt open; empty. He hated it. He felt Jensen’s big, warm body move between his legs, closer to his ass. His eyes flew open and he let go of his legs, letting them wrap around Jensen’s waist to pull him in closer.

Jensen pushed in slow, without stopping, until his hips were snug against Jared’s ass and Jared could feel the tickle of the hair on his balls against his spread open cheeks. He could feel the muscles in Jensen’s thighs tremble with the effort it took to hold still while Jared adjusted.

“Dean.” It was more of a breath than a plea, Jensen’s cock taking up most of the space in his body, not allowing air into his lungs. He didn’t have any words left to beg. His world was shrunk down to the feel of Jensen’s cock inside him and the word  _ DEAN _ reverberating through his head.

“I cant-I can’t hold back baby. Sammy, I gotta- I gotta.” With that, Jensen’s hips began to move, rocking back and forth slowly as he carved more space out of Jared’s body than Jared thought he had to spare.

His hips picked up speed, thrusting harder and faster and bigger with each thrust. The sound of slapping flesh overtook the sounds of their breathing. Jared was glad the talking had stopped; he couldn’t focus on anything more than the feel of Jensen’s cock. He needed it; he wanted it; he didn’t know how he’d lived without it.

He felt the pressure of his orgasm building and reached down to wrap his hand around the head of his cock. As soon as his fist closed around the head, he was coming. His back arched and his body tensed up and his eyes slammed closed again. He didn’t even realize he’d been yelling “Deandeandeandean” over and over again until he felt his throat start to hurt from it. When he finally opened his eyes and saw Jensen between his legs, muscles shining with sweat in the moonlight and still rocking his hips without ceasing, he knew what he needed.

“Come inside me Dean. Fill me up. I want it.”

Jensen’s hips fucked forward so hard that it hurt a little and Jared was sensitive enough that he could feel the throb and pulse of each spurt of come as Jensen emptied himself inside of him. Jensen held his hips still as he pulled away, both of them hissing at the oversensitivity. He could feel his hole gape open when Jensen’s cock pulled free and the trickle of come and lube as it dribbled out of him. He shivered and pulled Jensen down on top of him.

“Better than the first time, Dean?” He asked, suddenly unsure. Jensen lifted his head from where it was on his chest and blinked open his glassy-fucked out eyes.

“Better Sammy, cause it was our first time. We don’t need to be someone else to do this, do we Jay?” The role-play was over. Jared swallowed hard and cradled the back of Jensen’s sweaty head.

“Nah. Save it for special occasions, then?”

**Author's Note:**

> the fics that are mentioned and linked within the story are, in order:  
> Invisible Boy series by Dollylux (what are you even doing in spn/wincest fic if you haven't read it. DO IT)  
> The King and the Lionheart by Waywardelle (Best. Curtain. Fic. EVER. Do the thing, NOW)  
> I've Got a Hand for You by Edwardina (Scent kink, who fucking knew?)  
> I've got the Month of May by saltandbyrne (holy. shit. Weecest featuring jealous!bitch Sammy and seductive!Dean *sweats*)
> 
> All of the authors have given permission for their fics to be mentioned, with the exception of Edwardina... as I could not find her. Read them. Read them and fall in love like Jared (and I, we share the same taste in fic, who knew? lol).  
> AND COMMENT. Blessed are those who comment on fic.


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